Discover Luxury Houses and Villas in Siesta Key, FL

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Siesta Key, FL villas

Luxury Siesta Key, FL Vacation Houses and Villas

Spacious & Unique: Heated Pool ~ 2 Hot Tubs ~ Pkg! - Siesta Key, FL
9.6 62 reviews

Spacious & Unique: Heated Pool ~ 2 Hot Tubs ~ Pkg!

house, Siesta Key
Just 500 feet from the renowned Siesta Key beachfront, this pet-friendly 4BR duplex in the tranquil South Village district offers exclusive access and premium comfort.
Experience ultimate relaxation with two private pools, a hot tub, and complimentary WiFi, perfect for accommodating up to 16 guests.
The Beach Club At Siesta #102b - Siesta Key, FL
No reviews

The Beach Club At Siesta #102b

house, Siesta Key
Vacation rental listing. You will be located in Siesta Key.
Facilities and services include a dish washer, a swimming pool and air conditioning. This house in Siesta Key also has a terrace!
The Beach Club At Siesta #204b - Siesta Key, FL
10 1 review

The Beach Club At Siesta #204b

house, Siesta Key
Directly across from Crescent Beach, this luxury house offers unparalleled access to Siesta Key's shores.
Experience premium comfort with a fully equipped kitchen, on-site fitness center, and a private balcony overlooking the pool, accommodating up to 11 guests.
The Beach Club At Siesta #100d - Siesta Key, FL
9.3 3 reviews

The Beach Club At Siesta #100d

house, Siesta Key
Steps from Crescent Beach, this luxury house offers unparalleled access to Siesta Key's pristine sands and turquoise waters.
Experience premium comfort with a private hot tub, heated pool, and fitness center, accommodating up to 7 guests in this exclusive 600 sq ft retreat.
Sandy Seahorse Cottage - Siesta Key, FL
9.0 1 review

Sandy Seahorse Cottage

house, Siesta Key
Just 1,056 feet from Crescent Beach, Sandy Seahorse Cottage offers a luxury escape in Siesta Key.
This 6-bedroom, 5-bathroom accommodation boasts a private pool, balcony, and barbecue area, perfect for up to 46 guests.
Island House Beach Resort V28 - Siesta Key, FL
9.5 213 reviews

Island House Beach Resort V28

house, Siesta Key
Just steps from the Gulf of Mexico, this private villa in Siesta Key's Crescent Beach area offers direct beach access and proximity to Siesta Village.
Experience luxury and comfort in this standalone 1000 sq ft villa, featuring a fully equipped kitchen, private pool, tennis court, and resort amenities within the Island House Beach Resort community.
Siesta Key*private Beach*gulf Side*heated Pool - Siesta Key, FL
9.9 85 reviews

Siesta Key*private Beach*gulf Side*heated Pool

house, Siesta Key
Prime beachside on Siesta Key's Crescent Beach offers exclusive private beach access just a 2-minute walk away, with Stickney Point's dining and entertainment a short stroll from this luxury accommodation.
This premium 730 sq ft house, accommodating up to 4 guests, features a heated community pool, spa, tennis court, and a screened lanai with an electric grill for an exceptional beachside escape.
Gbb 1365 Watch Dolphins From Your Lanai In This Bayfront Siesta Key Condo - Siesta Key, FL
10 2 reviews

Gbb 1365 Watch Dolphins From Your Lanai In This Bayfront Siesta Key Condo

house, Siesta Key
Just a 7-minute walk from Crescent Beach, this luxury Siesta Key home offers an exclusive escape with a private sauna and lush garden setting.
Enjoy upscale comfort and year-round outdoor swimming in this welcoming 2-bedroom, 2-bathroom accommodation with free WiFi, perfect for up to 6 guests.

Luxury Houses and Villas in Downtown Siesta Key, FL

19 Premium Plus - Coastal Comfort - Siesta Key, FL
10 2 reviews

19 Premium Plus - Coastal Comfort

house, Siesta Key
Just 500 feet from Siesta Key Beach, this luxury villa offers exclusive access to over 200 feet of private beach.
Enjoy resort-style amenities including two swimming pools, tennis, pickleball, and shuffleboard courts, alongside convenient laundry facilities and nearby trolley access in Siesta Key.
Villa Vista Mare - 675 - Siesta Key, FL
10 8 reviews

Villa Vista Mare - 675

house, Siesta Key
Directly on the beach in Siesta Key, Villa Vista Mare offers unparalleled luxury just 600 feet from Siesta Key Beach and under a mile from Siesta Key Village.
This 2090 square foot house boasts three bedrooms, three bathrooms, and an on-site waterpark for an exclusive, premium experience.
Charming Beachside Retreat - Aloha Kai #18 - Roelens - Siesta Key, FL
10 1 review

Charming Beachside Retreat - Aloha Kai #18 - Roelens

house, Siesta Key
Directly steps away from Crescent Beach, this luxury beachside retreat in Siesta Key's Crescent Beach area offers effortless access to the shore and is approximately 8 miles from Marina Jack and the Sarasota Opera.
This exclusive 7530 square foot house boasts 1 bedroom, 1 bathroom, and accommodates up to 3 guests, featuring a fully equipped kitchen, spa, and waterpark for a premium, relaxing beach vacation.
Casa Mar 27 Studio Pool View - Steps To Beach - Siesta Key, FL
10 5 reviews

Casa Mar 27 Studio Pool View - Steps To Beach

house, Siesta Key
Directly on Siesta Key's Gulf of Mexico shoreline, this luxury studio offers unparalleled beach access mere steps from the soft white sands.
Experience a tranquil oasis with breathtaking pool views, featuring a queen-sized Murphy bed for optimal space and comfort, perfect for romantic getaways.

Luxury Villas with Private Pools in Siesta Key, FL

Among the 2040 accommodations in Siesta Key, FL, here are the 4 best villas and beach houses with a pool

Aloha Kai Villa 36 - Your Serene Siesta Key Retreat - Siesta Key, FL
No reviews

Aloha Kai Villa 36 - Your Serene Siesta Key Retreat

house, Siesta Key
Steps from Crescent Beach, Aloha Kai Villa 36 offers a luxury escape in Siesta Key, just 1.4 miles from Siesta Key Village.
This exclusive villa boasts a private heated pool and a fully equipped kitchen, perfect for your premium stay.
Beachside Bungalow - 1136 - Siesta Key, FL
No reviews

Beachside Bungalow - 1136

house, Siesta Key
Accommodation. You will stay in Siesta Key.
Facilities and services: a fridge, a washing machine and a dish washer. Take a dip in the pool of this house in Siesta Key!
Key West Villa 3 Min To #1 Beach  Pool  Bbq - Siesta Key, FL
9.5 64 reviews

Key West Villa 3 Min To #1 Beach Pool Bbq

house, Siesta Key
Just a 3-minute drive from Siesta Key Beach, this luxury villa in Siesta Retreats offers an exclusive getaway with a private heated pool.
Accommodating up to 6 guests, this premium 2-bedroom, 2-bathroom house features in-unit laundry and two private balconies for your comfort.
The Beach Club At Siesta #102a - Siesta Key, FL
10 1 review

The Beach Club At Siesta #102a

house, Siesta Key
Just 500 feet from Crescent Beach, this luxury house offers an exclusive getaway in Siesta Key with a fitness room and hot tub.
Experience premium comfort with a 800 sq ft floor plan accommodating up to 11 guests, featuring a private garden and tennis court.

Destinations nearby

Luxury Villas with a Jacuzzi in Siesta Key, FL

158 M² House ∙ 4 Bedrooms ∙ 8 Guests - Siesta Key, FL
10 8 reviews

158 M² House ∙ 4 Bedrooms ∙ 8 Guests

house, Siesta Key
Just a 10-minute walk to Siesta Key Village and a 15-minute walk to Siesta Key Beach, this private island retreat offers an exclusive Siesta Key luxury escape.
This 1690 sq ft house features a 2-bedroom main house and a detached 2-bedroom Casita, accommodating up to 8 guests with a private heated saltwater pool and hot tub.
60ft. Water Slide - Golf Simulator - Mini Golf - Siesta Key, FL
9.9 23 reviews

60ft. Water Slide - Golf Simulator - Mini Golf

house, Siesta Key
Just 500 feet from Siesta Key Beach's powdery white sand, this luxury house offers an exclusive Siesta Key escape.
This premium 6-bedroom, 6-bathroom accommodation comfortably hosts 18 guests with a private swimming pool, jacuzzi, and full kitchen.
6415 Midnight Pass #608 - Siesta Key, FL
No reviews

6415 Midnight Pass #608

house, Siesta Key
Just a 7-minute walk from Crescent Beach, this luxury house in Siesta Key offers a private terrace and year-round outdoor swimming pool.
This welcoming 1290 sq ft, 2-bedroom, 2-bathroom accommodation accommodates up to 11 guests with a fully equipped kitchen and on-site fitness center.
Home On Key With Pool, Hot Tub, Putting Green, Arcade Games, Bike & Mins To Beach! - Siesta Key, FL
No reviews

Home On Key With Pool, Hot Tub, Putting Green, Arcade Games, Bike & Mins To Beach!

house, Siesta Key
Less than a 20-minute walk from Siesta Key Beach, this luxury house offers an exclusive escape in Siesta Key.
This premium, 2600 sq ft home accommodates 42 guests with a private swimming pool, Jacuzzi, and on-site putting green for an unforgettable stay.

Luxury Vacation Homes with a Balcony in Siesta Key, FL

Pair luxury group living with breathtaking private vistas when you lock in a spectacular estate framing Siesta Key, FL.

Siesta Key Waterfront Estate Heated Pool Privacy! - Siesta Key, FL
9.3 72 reviews

Siesta Key Waterfront Estate Heated Pool Privacy!

house, South Sarasota
Secluded on one acre of waterfront with direct Gulf of Mexico access, this luxury house in South Sarasota provides an exclusive escape.
Enjoy a private heated swimming pool and on-site boating options at this tranquil, family-friendly retreat.
2bed/2bath Condo Next To Siesta Key ~A Hidden Gem - Siesta Key, FL
9.1 52 reviews

2bed/2bath Condo Next To Siesta Key ~A Hidden Gem

house, Gulf Gate Estates
Just 500 feet from Crescent Beach, this Gulf Gate Estates house offers a luxury escape with excellent ratings and private parking.
Enjoy a welcoming 2-bedroom, 2-bathroom layout accommodating 12 guests with air conditioning, a kitchenette, and access to an outdoor swimming pool.
6415 Midnight Pass #304 - Siesta Key, FL
No reviews

6415 Midnight Pass #304

house, Siesta Key
Just a 7-minute stroll from Crescent Beach, this luxury house in Siesta Key offers an exclusive escape with on-site waterpark fun.
This premium 1250 sq ft accommodation welcomes up to 11 guests with 2 bedrooms, 2 bathrooms, a private terrace, and a year-round outdoor pool.
Large Home, Private Pool, Arcade Lounge And Beach - Siesta Key, FL
10 2 reviews

Large Home, Private Pool, Arcade Lounge And Beach

house, Siesta Key
Just 1.5 miles from Siesta Key Beach, this luxury four-bedroom holiday home offers an exclusive escape with a private saltwater swimming pool and dedicated arcade lounge.
This upscale ${accommodationTypeName} in ${cityText} boasts 3000 square feet of living space, accommodating up to 19 guests with a sun terrace, garden, and EV charging.
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